Amine alkanoic acid

As to the origins of the major N compounds identified, it is possible that at least a portion of some of these compounds are pyrolysis products of amino acids, peptides, proteins, [18] and porphyrins (a component of chlorophyll), [19] or originate from the microbial decomposition of plant lignins and other phenolics in the presence of ammonia. [20] Of considerable interest are the identifications aromatic and aliphatic nitriles. Nitriles can be formed from amines with the loss of 2 H2, from amides with the loss of H20, and also by reacting n-alkanoic acid with NH3. [21] The detection of long-chain alkyl- and dialkyl-nitriles points to the presence in the soil or SOM of long-chain amines... 

We can appreciate that ionization of the carboxylie acid is affected by the electron-withdrawing inductive effect of the ammonium residue hence the increased acidity when compared with an alkanoic acid. Similarly, loss of a proton from the ammonium cation of the zwitterion is influenced by the electron-donating inductive effect from the carboxylate anion, which should make the amino group more basic than a typical amine. That this is not the case is thought to be a solvation effect (compare simple amines). 

Carboxy terminal amino acid or peptide thiols are prepared from various p-amino alcohols by conversion into a thioacetate (R2NHCHR1CH2SAc) via a tosylate followed by saponification.Several methods have been used to prepare N-terminal peptide thiols, the most common procedure is the coupling of (acetylsulfanyl)- or (benzoylsulfanyl)alkanoic acids or add chlorides with a-amino esters or peptide esters, followed by deprotection of the sulfanyl and carboxy groups. 8 16 Other synthetic methods include deprotection of (trit-ylsulfanyl)alkanoyl peptides, 1718 alkaline treatment of the thiolactones from protected a-sulfanyl acids, 19 and preparation of P-sulfanylamides (HSCH2CHR1NHCOR2, retro-thior-phan derivatives) from N-protected amino acids by reaction of P-amine disulfides with carboxylic acid derivatives, followed by reduction. 20,21 In many cases, the amino acid or peptide thiols are synthesized as the disulfides and reduced to the corresponding thiols by the addition of dithiothreitol prior to use. 

The acetylsulfanyl alkanoic acids can also be prepared by thioacetylation of the corresponding bromo derivatives,[101 acrylic add derivatives, 1516 or lactones.133 A fluorescent sulfanylalkanoyl fluorescein derivative was prepared by reaction of acetylsulfanylalkanoyl amine with fluorescein isothiocyanate, followed by deprotection of the thiol group. 1 ... 

Analogous to the use of chiral enoates (see previous section), a, -unsaturated carboxylic amides, prepared from chiral amines, may be utilized in asymmetric 1,4-additions. When Grignard reagents are added to unsaturated amides (21), derived from (-)-ephedrine (20),25 highly optically active fi-sub-stituted alkanoic acids (22 R and R = alkyl or phenyl) are obtained in a variety of cases, after hydrolysis of the initially formed adducts (Scheme 7). This method was used for the synthesis of the antibiotic (-) malyngolide and its stereoisomers.26 Recrystallization of the intermediate (saturated) amide was necess-... 

A stimulating development of urea alcoholysis has been demonstrated very recently for better AE, in an innovative integrated process that incorporates fatty ester hydrolysis to co-amino-alkanoic acids [44], Within the scope of this chapter, the most interesting step of this process is the recycling of waste alcohol, formed by the hydrolysis step, for urea alcoholysis. Dialkyl carbonate is produced together with ammonia thereafter, the ammonia is engaged in the amination reaction to obtain the amino acids. The overall process avoids the storage of NH3 that is necessary for the amination route, and transforms a waste product-the alcohol-into the valuable dialkyl carbonate. 

Recently fluorinated chains were also attached to amine based dendrimers, like PPI and poly(amido amine) (PAMAM), by means of ionic self assembly with semiperfluorinated alkanoic acids (Fig. 71, 216, 217). All dendrimer complexes 216 with perfluorinated alkanoic acids show SmA phases except the fifth generation dendrimer which shows a Colrec phase [378]. Also semiperfluorinated 4-alkoxybenzoic acids 217 [379] and mixed systems combining fluorinated and nonfluorinated alkanoic or benzoic acids (216, 217) have been reported [379-381]. In most cases layer structures (SmA) and for higher generation dendrimers also modulated SmA phases (Colrec phases) were observed. The layer thickness of the SmA phases of the mixed complexes 216 depends on the ratio of fluorinated and non-fluorinated acids, where smaller d values were observed for dendrimers with low Rp-content for Rp-rich dendrimers the more rigid Rp-chains provide... 

Aboofazeli, R., Lawrence, C. B., Wicks, S. R., and Lawrence, M. J. (1994), Investigations into the formation and characterization of phospholipid microemulsions. Part 3. Pseudo-ternary phase diagrams of systems containing water-lecithin-isopropyl myristate and either an alkanoic acid, amine, alkanediol, polyethylene glycol alkyl ether or alcohol as cosurfactant, Int. J. Pharm., Ill, 63-72. 

Resolution of diastereomeric amides by preparative HPLC has been developed for a-branched alkanoic acids, and has been employed to prepare dimethyl branched alkanes implicated in tsetse fly sexual communication (6). In much of our own work we have made use of fractional crystallization whereby racemic acids are converted to amides of either (R)- or (S)-ot-methylbenzylamine. These amines are available from Hexcel Corp., Zeeland, MI, and the diastereomeric amides can be analyzed for purity chromato-graphically. 

Scheme 68 Synthesis AT-naphtosultam-substituted alkanoic acid hydroxyamides and alkyl-amines...

A thermally induced ring closure of an imino-amine with an alkanoic acid proceeds in refluxing toluene containing a trace of acetic acid. 

Hydrazine and primary amines induce ring opening of the thiazole ring of 5,6-dihydrothiazolo[3,2-i][l,2,4]triazole-6-ones (105) forming the respective 2-([l,2,4]thiazol-2-yl)alkanoic acid hydrazides and amides (125) (Equation (23)) <83JPR869>. 

Amine oxides of the same kind are manufactured by reaction of alkanoic acids and their esters with N,N-dimethyl-l,3-propanediamine and subsequent oxidation of the amino amide by hydrogen peroxide [9] ... 

Long-chain alkanoic acids have a limited use as surfactants. They are very weak acids having a pH range between 5 and 6. They are soluble in most organic solvents but purely soluble in water. Alkali metals and short-chain amines as counterions yield water-soluble soaps which, as a result of hydrolysis, form with free acids the dispersible 1 1 or 1 2 association complexes, so-called "acid soaps". 

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